HCID 18923326, compound → HCID 18923549, compound

HRID 1900000Notes

Reaction equation

HRID 1900000 reaction equation
[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][C:13]3[C:18]([N:19]([C:21](=O)[CH3:22])[CH3:20])=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:24])[C:5]2=[N:4][C:3]=1[CH3:25].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Br:1][C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][C:13]3[C:18]([N:19]([CH2:21][CH3:22])[CH3:20])=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:24])[C:5]2=[N:4][C:3]=1[CH3:25]

Participants

4

Reactant 2

HCID 18923326HCID 18923326, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18923549HCID 18923549, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 3-bromo-8-[2-chloro-6-(N-acetyl-N-methylamino) benzyloxy]-2-methylimidazo[1,2-a]pyridine (103 mg) in tetrahydrofuran (2 ml) was added lithium aluminum hydride (16 mg) in several portions at 5° C. After the addition, the mixture was stirred for 2 hours at 5° C. and then quenched with aqueous saturated ammonium chloride solution. The separated organic layer was washed with aqueous saturated ammonium chloride solution, dried, and concentrated in vacuo. The residue was purified by preparative thin-layer chromatography (ethyl acetate:n-hexane =1:2, V/V) to give 3-bromo-8-[2-chloro-6-(N-ethyl-N-methylamino)benzyloxy]-2-methylimidazo[1,2-a]pyridine (41 mg).

Workup

  1. additionAfter the addition
  2. customquenched with aqueous saturated ammonium chloride solution
  3. washThe separated organic layer was washed with aqueous saturated ammonium chloride solution
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative thin-layer chromatography (ethyl acetate:n-hexane =1:2, V/V)

Sources & evidence

ORD record
ord-c9f1b71f56594230ab65ab29af603664
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

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